Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromopyridine-2-carboxamide

Example 10 Preparation of 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvcloheylamino)ethyl)picolinamide (Compound-46) and 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00144] 5-Bronnopicolinannide 112 (1.29 g, 6.4 mmol) and chloral (1.25 ml_) in dioxane (10 ml_) were heated to 100 0C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%). [00145] A solution of 5-bromo-N-(2,2,2-thchloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 0C for 30 minutes. The mixture was cooled to -78 0C and 4-ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Sitheta2), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1.80- 1.71 (m, 2H), 1.59-1.21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound- 47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1.86-1.70 (m, 4H), 1.27-1.01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5 ,Some common heterocyclic compound, 195044-14-5, molecular formula is C9H12BrN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (200 mg, 0.833 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (214 mg, 0.999 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (230 mg, 1.666 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (31 mg, 0.666 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (30 mg, 0.333 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 95% EtOAc/Hexane to afford 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 32.25%) as off white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,195044-14-5, its application will become more common.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate. A new synthetic method of this compound is introduced below., COA of Formula: C9H7BrN2O2

A mixture of methyl delta-bromo-lJ-diazabicyclo^^.OJnona^^^jdelta-tetraene-S-carboxylate (0.39 mmol, 100 mg), (6-dimethylaminopyridin-3-yl)boronic acid (0.59 mmol, 98 mg), cesium carbonate (1.57 mmol, 510 mg) and Pd(dppf)Cl2*DCM ( 39 mumol, 32 mg) was dissolved in DMF (3 ml). The mixture was stirred at 80 0C for 1 h and filtered. The filtrate lambdavas subjected to preparative HPLC to give 20 mg of the title compound as a white solid. IH NMR (400 MHz, DMSO-^6) delta ppm 9.24 (s, 1 H) 8.69 (d, J=2.02 Hz, 1 H) 8.38 (s, 1 H) 8.02 (dd, J=8.84, 2.27 Hz, 1 H) 7.61 (s, 2 H) 6.73 (d, J=8.84 Hz, 1 H) 3.89 (s, 3 H) 3.08 (s, 6 H); MS m/z (M+H) 297

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72648-12-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.72648-12-5, name is 2-Chloro-3-(trichloromethyl)pyridine, molecular formula is C6H3Cl4N, molecular weight is 230.91, as common compound, the synthetic route is as follows.

The 2-chloro-3-trichloromethylpyridine is hydrolyzed to obtain a 2-chloronicotinic acid reaction product, and the reaction formula is as follows

Statistics shows that 72648-12-5 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-3-(trichloromethyl)pyridine.

Reference:
Patent; Weifang Xinlv Chemical Co., Ltd.; Han Zengrui; Sun Zaichen; Han Zhiren; Zhang Jinwang; Jiang Dongsheng; (10 pag.)CN110229098; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6318-51-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone. A new synthetic method of this compound is introduced below.

0.2 g of (4-chlorophenyl) (2-pyridyl) methanone was dissolved in 2 mL of hydrogen peroxide (mass concentration of 30% aqueous solution) 1.0 mL of acetic acid was added and the reaction was heated to 85 C. for 12 h. The progress of the reaction was monitored by TLC until the reaction was complete. The mixture was saturated with sodium bicarbonate, extracted with dichloromethane, washed, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, Removal of the solvent gave 0.21 g of a white solid in 95% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, and friends who are interested can also refer to it.

Reference:
Patent; Yichang Renfu Pharmaceutical Co., Ltd.; China Three Gorges University; Fu Yigang; Lv Jinliang; Zhou Haifeng; Wang Baigui; Cao Lu; Zheng Huazhang; Tian Luanyuan; Li Shiqun; Li Lie; Du Wentao; (13 pag.)CN106938995; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 7477-10-3, name is 6-Chloro-5-nitronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Chloro-5-nitronicotinic acid

EXAMPLE 16 2-Fluoro-3- nitro-5-trifluoromethylpyridine/2-chloro-3-nitro-5-trifluoromethylpyridine mixture A steel bomb was charged with 6-chloro-5-nitronicotinic acid (4.1 g, 0.02 m), SF4 (21 g) and HF (3.7 ml). The mixture was heated at 90 for eight hours. After cooling to 25, the bomb was vented and the contents poured onto ice. The solution was neutralized with saturated Na2 CO3 solution and extracted with CH2 Cl2. The organic layer was dried over Na2 SO4, filtered and the solution was distilled. A mixture of 2-chloro and 2-fluoro-3-nitro-5-trifluoromethylpyridine (3.3 g) was obtained by distillation at 198-200 (760 mm).

With the rapid development of chemical substances, we look forward to future research findings about 7477-10-3.

Reference:
Patent; Merck & Co., Inc.; US4279913; (1981); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2897-43-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2897-43-0, name is 2,6-Dichloro-3-nitropyridin-4-amine, molecular formula is C5H3Cl2N3O2, molecular weight is 208, as common compound, the synthetic route is as follows.

(C) 2,6-dichloropyridi ne-3,4-diami ne[083] To a solution of 2,6-dichloro-3-nitropyridin-4-amine in ethanol (150 mL) was added iron powder (14.3 g, 0.255 mol), water (46 mL), and then concentrated HCI (28 mL). The reaction mixture was then stirred at 95 C for 16 hours, cooled to room temperature, and neutralized. The precipitates were collected by filtration and dried in vacuo. The crude product was then treated with water (200 mL) and extracted with EtOAc (3 x 200 mL). The combined extracts were dried over anhydrous Na2S04, filtered, and concentrated to afford 7.85 g of the title compound (86.5% yield).

Statistics shows that 2897-43-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-3-nitropyridin-4-amine.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; JI, Jianguo; WO2012/167423; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 1026796-81-5, blongs to pyridine-derivatives compound. COA of Formula: C7H7BrN2O

[00348] To a solution of N-(4-bromopyridin-2-yl)acetamide (350 mg, 1.6 mmol) in DCM (20 niL) was added mCPBA (1.26 g, 7.3 mmol) at 0C. The reaction mixture was allowed to stir at ii for 3 h. The reaction mixture was then diluted with water and saturated K2C03 solution, and extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The crude compound was purified by column chromatography to provide N-(4-bromo-1-oxidopyridin-2- yl)acetamide (340 mg, 90%). LCMS (FA): m/z 231.3 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; BHARATHAN, Indu T.; BLACKBURN, Chris; CIAVARRI, Jeffrey P.; CHOUITAR, Jouhara; CULLIS, Courtney A.; D’AMORE, Natalie; FLEMING, Paul E.; GIGSTAD, Kenneth M.; GIPSON, Krista E.; GIRARD, Mario; HU, Yongbo; LEE, Janice; LI, Gang; REZAEI, Mansoureh; SINTCHAK, Michael D.; SOUCY, Francois; STROUD, Stephen G.; VOS, Tricia J.; WONG, Tzu-Tshin; XU, He; XU, Tianlin; YE, Yingchun; WO2015/108861; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 947249-13-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 13.39 mmol) in 1 ,4-dioxane (60 mL) were added4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1 ,3,2-dioxaborolane) (3.74 g, 14.73 mmol),tricyclohexylphosphine (525 mg, 1.87 mmol), potassium acetate (3.28 g, 33.47 mmol) and tris(dibenzylideneacetone)dipalladium(0) (490 mg, 0.53 mmol). The reaction mixture was purged with nitrogen for 2 mm and heated to 110 C for 16 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were dried over sodium sulfate andconcentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25% ethyl acetate in hexane) affording 3-(difluoromethoxy)-5- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2-amine (1.3 g, 34%): 1H NMR (400 MHz, DMSO-d6) oe: 8.03 (s, 1H), 7.33 (s, 1H), 7.11 (t, I = 73.6 Hz, 1H),6.44 (s, 2H), 1.25 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-4-iodo-3-methylpyridine

N-((S)-1-(4-((R)-1-(2-Chloro-3-methylpyridin-4-yl)pyrrolidin-3-yloxy)phenyl)ethyl)acetamide Under inert gas atmosphere 0.80 g (2.53 mmol) of example XIII.1, 0.65 g (2.53 mmol) of 2-chloro-4-iodo-3-methyl-pyridine, 1.00 g (10.4 mmol) NaOtBu and 100 mg (0.14 mmol) chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)(2-(2-aminoethyl)-phenyl)-palladium (II) are added to 50 mL dioxane and stirred at 45 C. over night. Afterwards the solvent is removed, water is added and the product is extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (ACN/H2O/TFA). C20H24ClN3O2 (M=373.9 g/mol) ESI-MS: 374 [M+H]+Rt(HPLC):0.77 min (method M)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem